Basic information Safety Supplier Related

GERANYLGERANIOL

Basic information Safety Supplier Related

GERANYLGERANIOL Basic information

Product Name:
GERANYLGERANIOL
Synonyms:
  • Geranylgeraniol (Natural)
  • GERANYLGERANIOL
  • Geranylgeraniol (mixture of isomers)
  • 2,6,10,14-Hexadecatetraen-1-ol, 3,7,11,15-tetramethyl-, (2E,6E,10E)-
  • (2E,6E,10E)-3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetren-1-ol
  • (2E,6E,10E)-3,7,11,15-Tetramethylhexadecane-2,6,10,14-tetrene-1-ol
  • all-E-Geranylgeraniol
  • ALL TRANS-3,7,11,15-TETRAMETHYL-2,6,10,14-HEXADECATETRAEN-1-OL
CAS:
24034-73-9
MF:
C20H34O
MW:
290.48
Product Categories:
  • Miscellaneous Natural Products
  • Mixed Fatty Acids
  • Fatty Acid Derivatives & Lipids
  • Glycerols
Mol File:
24034-73-9.mol
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GERANYLGERANIOL Chemical Properties

Boiling point:
152-153 °C(Press: 0.07 Torr)
Density 
0.8930 g/cm3(Temp: 18 °C)
storage temp. 
-20°C
solubility 
Chloroform (Sparingly), Dichloromethane (Slightly), Ethyl Acetate (Slightly)
form 
liquid
pka
14.42±0.10(Predicted)
color 
Colourless to Light Yellow
BRN 
1913779
Stability:
Light Sensistive, Temperature Sensitive
InChI
InChI=1S/C20H34O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h9,11,13,15,21H,6-8,10,12,14,16H2,1-5H3/b18-11+,19-13+,20-15+
InChIKey
OJISWRZIEWCUBN-QIRCYJPOSA-N
SMILES
C(O)/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(/C)\C
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3
HS Code 
29052290

MSDS

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GERANYLGERANIOL Usage And Synthesis

Chemical Properties

Light Yellow Oil

Uses

A intermediate in the lipidation of proteins, which plays a great importance for a variety of biological processes such as cell signalling

Uses

Geranylgeraniol, a precursor to Geranylgeranylpyrophosphate (G367600), is an intermediate in the mevalonate pathway. Geranylgeraniol has been shown to prevent bone re-adsorption, inhibition of osteoclast formation, and kinase activation in vitro.

Definition

ChEBI: Geranylgeraniol is a diterpenoid that is hexadeca-2,6,10,14-tetraene substituted by methyl groups at positions 3, 7, 11 and 15 and a hydroxy group at position 1. It has a role as a plant metabolite, a volatile oil component and an antileishmanial agent. It is a diterpenoid and a polyprenol.

Biochem/physiol Actions

As the pyrophosphate, the metabolic precursor of all diterpenes. Screening in vitro shows this to be a potent and selective agent against Mycobacterium tuberculosis.

in vivo

Geranylgeraniol (725 mg/kg/d; p.o.; 90 d) is not toxicologically significant with a dose below 725 mg/kg/d in rats[3].
Geranylgeraniol (483 mg/kg/d; p.o.; 10 d) suppresses lipopolysaccharide-induced inflammation via inhibition of nuclear factor-κB activation in rats[4].

Animal Model:Han Wistar rats (169-192 g for male; 116-152 g for female)[3]
Dosage:0, 725, 1450, and 2900 mg/kg
Administration:Oral gavage; once daily; 90 days
Result:Showed the lowest observed adverse effect level (LOAEL) for local effects and the no observed adverse effect level (NOAEL) for systemic effects as 725 mg/kg/d.
Reduced body weights by 12.9 and 21.6% in the intermediate- and high-dose group males, respectively, compared to controls.
Animal Model:Wistar rats (male, 8-week-old, 130-150 g)[4]
Dosage:0, 48.3, 483, 4830 mg/kg
Administration:Oral gavage; once daily; 10 days; with or not LPS challenge (i.p.; 0.5 mg/kg)
Result:Suppressed LPS-induced inflammatory cytokines and mRNA expression of LPS-induced inflammatory genes in liver with doses of 483 mg/kg and 4830 mg/kg.
Suppressed protein levels of IRAK1, TRAF6, and TAK1, originating from transcriptional down-regulation with doses of 483 mg/kg and 4830 mg/kg.

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